Get new listings emailed daily! JOIN SIGN IN
Matthew Faul
Commercial & Residential Real Estate
(941) 345-3255
Facebook Icon LinkedIn Icon Twitter Icon 
Refine Search
$13,950,000

3440 Gulfmead Drive Sarasota, FL 34242 Residential - Single Family Active

  • 3440 Gulfmead Drive, Sarasota, FL 34242 Main Photo

83 Total Photos [Click to View All]

Description

Discover a rare opportunity to enjoy pristine Gulf views, aquamarine waters, and a deep-water dock on the very North end of Siesta Key, just minutes to downtown Sarasota. One of Siesta Key's most stunning and secluded waterfront sites - a residence offering a rare combination of historic significance, panoramic views of Big Pass, and exceptional structural integrity. Located approximately 200 feet south of civic leader Henry Higel's early 20th-century Higelhurst Hotel, the pioneering developer's beloved coastal breezes still beckon family and friends to enjoy swimming, water sports, boating, fishing, shoreline picnics, and direct, no-bridge access to the sparkling Gulf. Multiple covered porches and expansive windows provide front-row views of vivid sunsets and frolicking dolphins. Named for its pineapple stair finials symbolizing welcome, the Pineapple House was built in 2008 with an engineer-homeowner's meticulous eye for detail. Constructed on pilings and grade beams, the home is set on a 31,293-square-foot lot and encompasses 6,596 square feet under air, with more than 13,000 total square feet. Designed by Diane Weinman with a refined Boca Grande aesthetic and built by ML Collingwood, the dwelling projects enduring quality, thoughtful engineering, and elevated coastal living. Enter through the impressive double doors to a sensual treat of symmetry and light. Main-level windows crowned with transoms frame views of the tropical blue sky. Walnut engineered flooring, Jerusalem stone, eight-foot doors, custom millwork, and generous closets enhance both functionality and beauty throughout. Scaled to feel both warm and elegant, the interiors are enriched with refined finishes and thoughtful architectural detailing. Living spaces encompass a formal dining room with butler's pantry, living room, bookcase-lined library or sitting room, private office with built-in desk and cabinetry, dedicated home gym, and a flexible gathering room. A second primary or guest suite on the main level offers a private sitting area, breakfast bar, screened porch, and picture-perfect water views. An elevator conveniently serves all three floors. The chef's kitchen anchors the main living areas with honed granite countertops, Sub-Zero appliances, custom Campbell cabinetry, and a walk-in pantry, opening to casual dining spaces and sun-filled outdoor porches. Upstairs, the primary suite is a tranquil retreat featuring a spa-inspired bath, oversized walk-in closet, shaded terrace, and outdoor shower. The expansive dock features two boat lifts: one 22,000-pound lift suitable for a 32- to 36-foot vessel and a second 10,000-pound lift. A humidity-controlled four-car tandem garage and a separate two-car garage accommodate up to six vehicles along with extensive marine and recreational gear. Solar panels and a 30kW generator underscore the home's focus on energy efficiency and resilience. Outdoor living is highlighted by a 20,000-gallon heated saltwater lap pool surrounded by Shellcrete patios and Ipe decking. A perched beach with fire pit and swings welcomes gatherings overlooking Big Pass, while a 75-foot rear setback ensures privacy within a lushly landscaped yard. Rich in history, resilient and luxurious, intimate and refined, this is Sarasota waterfront living at its most authentic and coveted.

Property Highlights

Property Type: Residential - Single Family
Cooling: Central Air, Zoned
Fenced: Yes
Garage: 6 car attached
Heating: Central, Electric, Zoned
Home Style: Custom, Florida
Lot Size: 0.72 Acres
Roof Type: Metal
Stories: 3.0
Taxes: $58,420
Year Built: 2008

General Information

Bedrooms: 5
Bathrooms: 4 Full 2 Half
Sqft: 6,596
County: Sarasota
Subdivision: GULFMEAD ESTATES
Listed By:
Jennifer Linehan MICHAEL SAUNDERS & COMPANY 941-951-6660

Amenities

Built-in Features
Ceiling Fans(s)
Crown Molding
Eat-in Kitchen
Elevator
High Ceilings
Open Floorplan
PrimaryBedroom Upstairs
Solid Wood Cabinets
Split Bedroom
Stone Counters
Thermostat
Vaulted Ceiling(s)
Walk-In Closet(s)
Wet Bar
Window Treatments
French Doors
Lighting
Outdoor Shower
Rain Gutters

Room Information

Living Room: 17x29
Kitchen: 20x18
Dinette: 21x16
Dining Room: 17x14
Library: 17x13
Office: 14x14
Bedroom 2: 21x14
Primary Bedroom: 18x17
Bedroom 3: 16x14
Bedroom 4: 11x20
Bedroom 5: 13x18

Property Features

Additional Rooms: Attic, Breakfast Room Separate, Den/Library/Office, Family Room, Formal Dining Room Separate, Formal Living Room Separate, Inside Utility, Interior In-Law Suite w/Private Entry, Storage Rooms
Appliances: Bar Fridge, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Ice Maker, Kitchen Reverse Osmosis System, Microwave, Range, Range Hood, Refrigerator, Washer, Water Filtration System, Water Softener, Wine Refrigerator
Body of Water: BIG PASS
Builder: ML Collingwood
Community Features: Street Lights
Days on Site: 25
Directions: Siesta Drive straight to Gulfmead Drive. Follow road to the right and the home is the third on the left.
Energy Efficient: Insulation, Water Heater, Windows
Exterior: Block, Concrete, Stucco
Fencing: Fenced
Fireplace: Living Room, Wood Burning
Fireplace Y/N: Yes
Flood Zone Code: AE
Flooring: Brick, Other, Wood
Foundation: Stilt/On Piling
Frontage Gulf Ocean: 100
Garage Dimensions: 26x41
Home Warranty Y/N: No
Listing Terms: Cash, Conventional
Lot: FloodZone, City Limits, Landscaped, Street Dead-End, Paved
Lot Dimensions: 0.72
Number of Wells: 1
Other Equipment: Irrigation Equipment
Ownership: Fee Simple
Parking: Tandem, Workshop in Garage
Parking Notes: Tandem, Workshop in Garage
Patio/Porch: Covered, Enclosed, Rear Porch, Screened, Side Porch, Wrap Around
Pets Allowed: Yes
Pool: In Ground, Lap, Salt Water
Property Attached Y/N: No
Property Sub-Type: Single Family Residence
Security: Closed Circuit Camera(s), Fire Alarm, Security System, Security System Owned, Smoke Detector(s)
Sewer: Public Sewer
Showing Instructions: 24 Hour Notice, Listing Agent Must Accompany
Special Sale Provisions: None
Special View Info: Water
Swimming Pool: Yes
Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Available, Propane, Sewer Connected, Sprinkler Well, Water Connected
Vegetation: Mature Landscaping, Trees/Landscaped
Water: Public, Well
Water Access: Gulf/Ocean to Bay
Water Access Y/N: Yes
Waterfront Features: Gulf/Ocean, Lift, Riprap, Sailboat Water, Seawall - Concrete
Water View: Gulf/Ocean - Full
Windows: Drapes, Rods, Storm Window(s)
Zoning: RSF1
$13,950,000
5beds
4.5baths
6,596sqft
6cars
Active
BEDS5 BATHS4 full 2 partial SQUARE FEET6,596 MLS#A4679384
STATUSActive PROPERTY TYPEResidential - Single Family SUBDIVISIONGULFMEAD ESTATES

Get in Touch

Contact an agent to learn more about

3440 Gulfmead Drive, Sarasota, FL 34242.

Contact Form

Preferred Communication Method:

Estimate Your Payment

Estimated Payment

$ 55,988.09 per month $47,051.01 Principal & Interest $4,868.33 Property Tax $4,068.75 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)

About this area

Florida/Sarasota
Sarasota

View Listings

About Sarasota

Sarasota, FL is a cultural gem. Once home to the Ringling Brothers Circus, Sarasota boasts a rich arts scene that brings people from all over the area to enjoy world-class theater, music, and other performing arts. Sarasota is also a haven with spectacular scenery, turquoise water and white sandy beaches. It offers a delightful downtown with a variety of small boutiques and exceptional restaurants. With its dynamic culture and arts scene and incredible natural beauty, Sarasota is a wonderful place to call “home.” 

Learn More About Living in Sarasota, Florida

About this community

Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 03/03/2026. The listing information on this page last changed on 03/03/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 03/03/2026 12:32:12 AM EST) or Stellar MLS (last updated Tue 03/03/2026 12:14:05 AM EST). Real estate listings held by brokerage firms other than Wagner Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

Listing data and photos distributed by MLSGRID
Member Participants (and their affiliated licensees, if applicable) shall indicate on their websites that IDX information is provided exclusively for consumers’ personal non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, that the data is deemed reliable but is not guaranteed by MLS GRID, and that the use of the MLS GRID Data may be subject to an end user license agreement prescribed by the Member Participant’s applicable MLS if any and as amended from time to time. MLS GRID may, at its discretion, require use of other disclaimers as necessary to protect Member Participant, and/or their MLS from liability.
Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.



Privacy Policy / DMCA Notice / ADA Accessibility

Login to My Homefinder

Pixel